Organic Letters
Letter
Org. Lett. 2016, 18, 1594−1597. (r) Friedfeld, M. R.; Zhong, H.; Ruck,
R. T.; Shevlin, M.; Chirik, P. Science 2018, 360, 888−893.
(4) (a) Hamada, Y.; Koseki, Y.; Fujii, T.; Maeda, T.; Hibino, T.;
Makino, K. Chem. Commun. 2008, 46, 6206−6208. (b) Hibino, T.;
Makino, K.; Sugiyama, T.; Hamada, Y. ChemCatChem 2009, 1, 237−
240.
AUTHOR INFORMATION
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Corresponding Author
ORCID
(5) (a) Yang, P.; Xu, H.; Zhou, J. Angew. Chem., Int. Ed. 2014, 53,
12210−12213. (b) Guo, S.; Yang, P.; Zhou, J. Chem. Commun. 2015,
51, 12115−12117. (c) Guo, S.; Zhou, J. Org. Lett. 2016, 18, 5344−
5347. (d) Xu, H.; Yang, P.; Chuanprasit, P.; Hirao, H.; Zhou, J. Angew.
Chem., Int. Ed. 2015, 54, 5112−5116. (e) Yang, P.; Lim, L. H.;
Chuanprasit, P.; Hirao, H.; Zhou, J. Angew. Chem., Int. Ed. 2016, 55,
12083−12087.
Notes
The authors declare no competing financial interest.
ACKNOWLEDGMENTS
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(6) Shevlin, M.; Friedfeld, M. R.; Sheng, H.; Pierson, N. A.; Hoyt, J.
M.; Campeau, L.-C.; Chirik, P. J. J. Am. Chem. Soc. 2016, 138, 3562−
3569.
We are grateful for financial support from the National Natural
Science Foundation of China (Grant Nos. 21871212, 21402145,
21432007), the Natural Science Foundation of Hubei Province
(2018CFB430), the Fundamental Research Funds for the
Central Universities (2042017kf0177), the Important Sci-Tech
Innovative Project of Hubei Province (2015ACA058), and the
“111” Project of the Ministry of Education of China.
(7) Chen, F.; Zhang, Y.; Yu, L.; Zhu, S. Angew. Chem. 2017, 129,
2054−2057.
(8) (a) Reading, C.; Cole, M. J. Enzyme Inhib. 1986, 1, 83−104.
(b) Nottingham, M.; Bethel, C. R.; Pagadala, S. R. R.; Harry, E.; Pinto,
A.; Lemons, Z. A.; Drawz, S. M.; van den Akker, F.; Carey, P. R.;
Bonomo, R. A.; Buynak, J. D. Bioorg. Med. Chem. Lett. 2011, 21, 387−
393. (c) Sandanayaka, V. P.; Prashad, A. S.; Yang, Y.; Williamson, R. T.;
Lin, Y. I.; Mansour, T. S. J. Med. Chem. 2003, 46, 2569−2571.
(d) Salmas, R. E.; Seeman, P.; Aksoydan, B.; Erol, I.; Kantarcioglu, I.;
Stein, M.; Yurtsever, M.; Durdagi, S. ACS Chem. Neurosci. 2017, 8,
1404−1415. (e) Annes, W. F.; Long, A.; Witcher, J. W.; Ayan-Oshodi,
M. A.; Knadler, M. P.; Zhang, W.; Mitchell, M. I.; Cornelissen, K.; Hall,
S. D. J. Pharm. Sci. 2015, 104, 207−214. (f) Mehta, M. A.; Schmechtig,
A.; Kotoula, V.; McColm, J.; Jackson, K.; Brittain, C.; Tauscher-
Wisniewski, S.; Kinon, B. J.; Morrison, P. D.; Pollak, T.; Mant, T.;
Williams, S. C. R.; Schwarz, A. J. Psychopharmacology 2018, 235, 1875−
1886. (g) Reed, M.; Crosbie, D. Ther. Adv. Musculoskeletal Dis. 2017, 9,
45−53.
REFERENCES
■
(1) For selected reviews for recent advances on transition-metal-
catalyzed asymmetric hydrogenation, see: (a) Xie, J.; Zhu, S.; Zhou, Q.
Chem. Rev. 2011, 111, 1713−1760. (b) Ager, D. J.; de Vries, A. H. M.;
de Vries, J. G. Chem. Soc. Rev. 2012, 41, 3340−3380. (c) Liu, Y.; Wang,
Z.; Ding, K. Huaxue Xuebao 2012, 70, 1464−1470. (d) Xie, J.; Zhou, Q.
Huaxue Xuebao 2012, 70, 1427−1438. (e) Wang, D.-S.; Chen, Q.-A.;
Lu, S.-M.; Zhou, Y.-G. Chem. Rev. 2012, 112, 2557−2590. (f) Verendel,
̀
́
J. J.; Pamies, O.; Dieguez, M.; Andersson, P. G. Chem. Rev. 2014, 114,
2130−2169. (g) Zhang, Z.; Butt, N. A.; Zhang, W. Chem. Rev. 2016,
116, 14769−14827. (h) Kraft, S.; Ryan, K.; Kargbo, R. B. J. Am. Chem.
Soc. 2017, 139, 11630−11641. (i) Meemken, F.; Baiker, A. Chem. Rev.
2017, 117, 11522−11569. (j) Zhu, S.; Zhou, Q. Acc. Chem. Res. 2017,
50, 988−1001. (k) Margarita, C.; Andersson, P. G. J. Am. Chem. Soc.
2017, 139, 1346−1356. (l) Zhu, S.; Zhou, Q. Acc. Chem. Res. 2017, 50,
988−1001.
(9) (a) Carretero, J. C.; Arrayas, R. G. J. Org. Chem. 1998, 63, 2993−
3005. (b) Alonso, D. A.; Costa, A.; Mancheno, B.; Najera, C.
Tetrahedron 1997, 53, 4791−4814. (c) Enders, D.; Mu
̈
ller, S. F.; Raabe,
ller, S.
G. Angew. Chem., Int. Ed. 1999, 38, 195−197. (d) Enders, D.; Mu
̈
F.; Raabe, G.; Runsink, J. Eur. J. Org. Chem. 2000, 2000, 879−892.
(10) (a) Kumareswaran, R.; Hassner, A. Tetrahedron: Asymmetry
2001, 12, 2269−2276. (b) Kumareswaran, R.; Balasubramanian, T.;
Hassner, A. Tetrahedron Lett. 2000, 41, 8157−8162. (c) Balasubrama-
nian, T.; Hassner, A. Tetrahedron: Asymmetry 1998, 9, 2201−2205.
(2) (a) Knowles, W. S. Acc. Chem. Res. 1983, 16, 106−112. (b) Noyori,
R.; Hashiguchi, S. Acc. Chem. Res. 1997, 30, 97−102. (c) Tang, W.;
Zhang, X. Chem. Rev. 2003, 103, 3029−3070. (d) Gridnev, I. D.;
Imamoto, T. Acc. Chem. Res. 2004, 37, 633−644. (e) Roseblade, S. J.;
Pfaltz, A. Acc. Chem. Res. 2007, 40, 1402−1411. (f) Zhou, Y. Acc. Chem.
Res. 2007, 40, 1357−1366. (g) Shimizu, H.; Nagasaki, I.; Matsumura,
K.; Sayo, N.; Saito, T. Acc. Chem. Res. 2007, 40, 1385−1393. (h) Zhang,
W.; Chi, Y.; Zhang, X. Acc. Chem. Res. 2007, 40, 1278−1290. (i) He, Y.;
Feng, Y.; Fan, Q. Acc. Chem. Res. 2014, 47, 2894−2906.
(3) (a) Sui-Seng, C.; Freutel, F.; Lough, A. J.; Morris, R. H. Angew.
Chem., Int. Ed. 2008, 47, 940−943. (b) Morris, R. H. Chem. Soc. Rev.
2009, 38, 2282−2291. (c) Mikhailine, A.; Lough, A. J.; Morris, R. H. J.
Am. Chem. Soc. 2009, 131, 1394−1395. (d) Zhou, S. L.; Fleischer, S.;
Junge, K.; Das, S.; Addis, D.; Beller, M. Angew. Chem., Int. Ed. 2010, 49,
8121−8125. (e) Lagaditis, P. O.; Lough, A. J.; Morris, R. H. J. Am.
Chem. Soc. 2011, 133, 9662−9665. (f) Sonnenberg, J. F.; Coombs, N.;
Dube, P. A.; Morris, R. H. J. Am. Chem. Soc. 2012, 134, 5893−5899.
(g) Mikhailine, A.; Maishan, M. I.; Lough, A. J.; Morris, R. H. J. Am.
Chem. Soc. 2012, 134, 12266−12280. (h) Monfette, S.; Turner, Z. R.;
Semproni, S. P.; Chirik, P. J. J. Am. Chem. Soc. 2012, 134, 4561−4564.
(i) Friedfeld, M. R.; Shevlin, M.; Hoyt, J. M.; Krska, S. W.; Tudge, M.
T.; Chirik, P. J. Science 2013, 342, 1076−1080. (j) Zuo, W. W.; Lough,
A. J.; Li, Y. F.; Morris, R. H. Science 2013, 342, 1080−1083. (k) Li, Y. Y.;
Yu, S. L.; Wu, X. F.; Xiao, J. L.; Shen, W. Y.; Dong, Z. R.; Gao, J. X. J. Am.
Chem. Soc. 2014, 136, 4031−4039. (l) Lagaditis, P. O.; Sues, P. E.;
Sonnenberg, J. F.; Wan, K. Y.; Lough, A. J.; Morris, R. H. J. Am. Chem.
Soc. 2014, 136, 1367−1380. (m) Li, Y. Y.; Yu, S. L.; Shen, W. Y.; Gao, J.
X. Acc. Chem. Res. 2015, 48, 2587−2598. (n) Morris, R. H. Acc. Chem.
Res. 2015, 48, 1494−1502. (o) Chirik, P. J. Acc. Chem. Res. 2015, 48,
1687−1695. (p) Bigler, R.; Huber, R.; Mezzetti, A. Angew. Chem., Int.
Ed. 2015, 54, 5171−5174. (q) Chen, J. H.; Chen, C. H.; Ji, C. L.; Lu, Z.
́
(d) Velazquez, F.; Arasappan, A.; Chen, K.; Sannigrahi, M.;
Venkatraman, S.; McPhail, A. T.; Chan, T. M.; Shih, N. Y.; Njoroge,
F. G. Org. Lett. 2006, 8, 789−792. (e) Zhang, H.; Li, Y.; Xu, W.; Zheng,
W.; Zhou, P.; Sun, Z. Org. Biomol. Chem. 2011, 9, 6502−6505.
(11) Jiang, J.; Wang, Y.; Zhang, X. ACS Catal. 2014, 4, 1570−1573.
(12) Gao, W.; Lv, H.; Zhang, T.; Yang, Y.; Chung, L. W.; Wu, Y.-D.;
Zhang, X. Chem. Sci. 2017, 8, 6419−6422.
(13) Li, X.; You, C.; Li, S.; Yang, Y.; Lv, H.; Zhang, X. Org. Lett. 2017,
19, 5130−5133.
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